Methyl iodide → 3-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-4-methyl-1,2,4-oxadiazol-5-one

HRID 1528344Notes

Reaction equation

HRID 1528344 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)\[C:11]2[NH:15][C:14](=[O:16])[O:13][N:12]=2)[N:6]=1.[C:23](=O)([O-])[O-].[K+].[K+].IC>CC#N.CN(C=O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)\[C:11]2[N:15]([CH3:23])[C:14](=[O:16])[O:13][N:12]=2)[N:6]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1366263593-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-4H-1,2,4-oxadiazol-5-one

Product 1

HCID 894440593-[(Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-C-phenylcarbonimidoyl]-4-methyl-1,2,4-oxadiazol-5-oneYield 61.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-1,2,4-oxadiazol-5(4H)-one (2.89 g, 50% purity, 4.56 mmol, 1 eq.) in MeCN (50 ml) and DMF (10 ml) was added potassium carbonate (757 mg, 5.48 mmol, 1.2 eq.) followed by iodomethane (778 mg, 5.48 mmol, 1.2 eq.). The reaction was stirred at room temperature overnight. The reaction was quenched by addition of water and extracted with EtOAc (3×50 ml). The organics were combined, washed with aq. sat. NaCl, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 3-[(Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)methyl]-4-methyl-1,2,4-oxadiazol-5(4H)-one (930 mg, 61% yield) has a white solid.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with EtOAc (3×50 ml)
  3. washwashed with aq. sat. NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f93b6c0232af44d79f65dd0bffb0a7e1
Source dataset
uspto-grants-2015_07
Patent number
US09090600B2

Reaction notes

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